Get access

Enantioselective Formal Total Syntheses of Didehydrostemofoline and Isodidehydrostemofoline through a Catalytic Dipolar Cycloaddition Cascade


  • We thank the National Institutes of Health (GM 25439 and GM 31077) and The Robert A. Welch Foundation (F-0652) for their generous support. D.H.P. thanks NIH for a postdoc fellowship (GM096557).


original image

Sweet to the core: Enantioselective formal total syntheses of the title compounds were accomplished in 24 steps from 2-deoxy-D-ribose. The synthesis features a novel cascade of reactions culminating in an intramolecular dipolar cycloaddition to form the tricyclic core of the stemofoline alkaloids from an acyclic diazo imine intermediate.

Get access to the full text of this article